Aluminum-Centered C–C Heterocoupling of Organonitriles

The <i>C-tert-</i>butyl substituted azacyclopropenylaluminate, [(SiN<sup>Dipp</sup>)-Al-η<sup>2</sup>-{NC<i>t</i>-Bu}-K]<sub>∞</sub> (SiN<sup>Dipp</sup> = (CH<sub>2</sub>SiMe<sub>2</sub>NDipp)<sub>2</sub>) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C-C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of <i>t</i>-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N<i>C</i> substituents.

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Publication Details

Journal
Organometallics
Published
2025-10-10
DOI
https://doi.org/10.1021/acs.organomet.5c00335
Primary Topic
Catalytic Cross-Coupling Reactions
Type
article
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article

Aluminum-Centered C–C Heterocoupling of Organonitriles

Aparna M. Thomas, Rex S. C. Charman, Kyle G. Pearce, Michael S. Hill et al.
Organometallics
Catalytic Cross-Coupling Reactions
article

Aluminum-Centered C–C Heterocoupling of Organonitriles

Aparna M. Thomas, Rex S. C. Charman, Kyle G. Pearce, Michael S. Hill, Louis J. Morris, Estelle M. Bouchat
article en

Abstract

The <i>C-tert-</i>butyl substituted azacyclopropenylaluminate, [(SiN<sup>Dipp</sup>)-Al-η<sup>2</sup>-{NC<i>t</i>-Bu}-K]<sub>∞</sub> (SiN<sup>Dipp</sup> = (CH<sub>2</sub>SiMe<sub>2</sub>NDipp)<sub>2</sub>) reacts with both aryl- and alkyl-substituted nitriles. In contrast to previously reported attempts to effect C-C bond formation between two dissimilar nitriles, these reactions enable the completely discriminating heterocoupling of <i>t</i>-BuCN to provide diazabutadienylaluminate dianions that bear two differentiated N<i>C</i> substituents.

OrganometallicsVol. 44(20)
University of Bath (GB)
Openalex Percentile: Top 78%
Catalytic Cross-Coupling Reactions
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